Jeremy Gilbert

For a while there, Jeremy Gilbert was a moody mess. After his parents’ death, he fell off the delinquent end and became one of Mystic Falls’ druggie outcasts. He’s since reformed his ways, but he still has a whole lot of drama.

For example, he’s terribly unlucky in love. Both of his Season 1 girlfriends were killed. Stefan staked the little Gilbert’s first love, town bad girl Vicki Donovan, after Damon turned her into a vampire. His Uncle John killed Jeremy’s second boo, the teen vamp Anna. Luckily, his third main squeeze, Bonnie — a wicked cool witch — seems to have bucked this trend, managing to die only temporarily, thanks to her spell-casting abilities.

Jeremy’s had some issues with older sis, Elena, as well. First, they are actually cousins, since E’s birth father was actually her Uncle John. Next, she spent the majority of Season 1 dodging questions about Mystic Falls’ mysteries and getting her vampy friends to modify her bro’s memory.

Now that Jer’s clued in to supernatural side, he’s eager to help, although his only real superpowers are the Gilbert ring — which protects him from death by supernatural spookies — and the ability to see ghosts.

Unfortunately, guns are not supernatural, and when Sheriff Forbes got a little trigger happy trying to shoot Damon, she hit Jeremy instead. Once again, Bonnie came to the rescue and revived her beau using the power of 100 witches. That’s when his sixth sense came into play.

In Season 3, Jeremy got a little too into ghosts, cheating on Bonnie with the ethereal Anna. After Klaus (Joseph Morgan) nearly kills Jeremy through compulsion, Elena has Damon compel him and send him to Denver. Upon his return, Jeremy attempts to get his sister out of town, inadvertently leading to her death/vampirism.

Fast facts:

1. Jeremy has killed a hybrid by removing its head. Future hunter in the making?

2. The character of Jeremy Gilbert does not exist in The Vampire Diaries novels by L.J. Smith. Instead Elena had a little sister named Margaret.

3. Apparently, Jeremy is quite the artist and sketches all kinds of creatures of the night in his picto-journal.